Co-Metal-Free Enantioselective Conjugate Addition Reactions of Zinc Reagents

被引:27
作者
Ay, Sefer [1 ]
Nieger, Martin [2 ]
Braese, Stefan [1 ]
机构
[1] Univ Karlsruhe, Inst Organ Chem, D-76131 Karlsruhe, Germany
[2] Univ Helsinki, Inorgan Chem Lab, FIN-00014 Helsinki, Finland
关键词
asymmetric catalysis; conjugate addition reactions; enals; N; O-ligands; organozinc reagents;
D O I
10.1002/chem.200801676
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Asymmetric conjugate addition of diethylzine to cinnamaldehyde in a co-metal-free fashion by using N,O-ligands with planar and central chirality is described. Different modulations of the ligand structure, including several combinations of the chiral units. indicate that a [2.2]paracyclophane backbone is essential for the activity and the enantioselectivity of the generated active catalyst. By using the optimized ligand, an isolated yield of 90% was obtained with up to 99% ee.
引用
收藏
页码:11539 / 11556
页数:18
相关论文
共 117 条
[61]   Effect of InCl3 on the addition of Grignard reagents to α,β-unsaturated carbonyl compounds [J].
Kelly, BG ;
Gilheany, DG .
TETRAHEDRON LETTERS, 2002, 43 (05) :887-890
[62]   ENANTIOSELECTIVE ADDITION OF DIALKYLZINCS TO ALDEHYDES PROMOTED BY CHIRAL AMINO-ALCOHOLS - MECHANISM AND NONLINEAR EFFECT [J].
KITAMURA, M ;
OKADA, S ;
SUGA, S ;
NOYORI, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (11) :4028-4036
[63]  
Krause N, 2001, SYNTHESIS-STUTTGART, P171
[64]   Synthesis of novel planar-chiral [2.2]paracyclophane derivatives as potential ligands for asymmetric catalysis [J].
Kreis, Michael ;
Nieger, Martin ;
Braese, Stefan .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (10) :2171-2181
[65]   TRANSITION-METAL CATALYZED OXIDATIONS .3. REACTION OF 4-HYDROXY[2.2]PARACYCLOPHANE WITH THE MIMOUN MOLYBDENUM OXODIPEROXO COMPLEX [MO(O2)2O].PY.HMPT [J].
KROHN, K ;
RIEGER, H ;
HOPF, H ;
BARRETT, D ;
JONES, PG ;
DORING, D .
CHEMISCHE BERICHTE, 1990, 123 (08) :1729-1732
[66]   Asymmetric syntheses of 2-(1-aminoethyl)phenols [J].
Kündig, EP ;
Botuha, C ;
Lemercier, G ;
Romanens, P ;
Saudan, L ;
Thibault, S .
HELVETICA CHIMICA ACTA, 2004, 87 (03) :561-579
[67]   Planar- and central-chiral N,O-[2.2]paracyclophane ligands:: Non-linear-like effects and activity [J].
Lauterwasser, F ;
Vanderheiden, S ;
Bräse, S .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (4-5) :443-448
[68]   Structurally diverse second-generation [2.2]paracyclophane ketimines with planar and central chirality:: Syntheses, structural determination, and evaluation for asymmetric catalysis [J].
Lauterwasser, F ;
Nieger, M ;
Mansikkamäki, H ;
Nättinen, K ;
Bräse, S .
CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (15) :4509-4525
[69]   Second-generation N,O-[2.2]paracyclophane ketimine ligands for the alkenylzinc addition to aliphatic and aromatic aldehydes:: Scope and limitations [J].
Lauterwasser, Frank ;
Gall, Julia ;
Hoefener, Sebastian ;
Braese, Stefan .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (15) :2068-2074
[70]   Copper-catalyzed enantioselective conjugate addition of Grignard reagents to α,β-unsaturated esters [J].
López, F ;
Harutyunyan, SR ;
Meetsma, A ;
Minnaard, AJ ;
Feringa, BL .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (18) :2752-2756